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Novel Bicyclic P,S-Heterocycles via Stereoselective hetero-Diels-Alder Reactions of Thiochalcones with 1-Phenyl-4H-phosphinin-4-one 1-Oxide.
Mloston, Grzegorz; Urbaniak, Katarzyna; Palusiak, Marcin; Lastawiecka, Elzbieta; Frynas, Slawomir; Pietrusiewicz, Kazimierz Michal; Heimgartner, Heinz.
Afiliación
  • Mloston G; Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland.
  • Urbaniak K; Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland.
  • Palusiak M; Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland.
  • Lastawiecka E; Department of Organic and Crystal Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Gliniana 33, 20-614 Lublin, Poland.
  • Frynas S; Department of Organic and Crystal Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Gliniana 33, 20-614 Lublin, Poland.
  • Pietrusiewicz KM; Department of Organic and Crystal Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Sklodowska University, Gliniana 33, 20-614 Lublin, Poland.
  • Heimgartner H; Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.
Molecules ; 29(9)2024 Apr 28.
Article en En | MEDLINE | ID: mdl-38731526
ABSTRACT
Thiochalcones undergo cycloaddition reactions in THF solution at 60 °C with the synthetically unexplored 1-phenyl-4H-phosphinin-4-one 1-oxide in a highly regio- and stereoselective manner, yielding hitherto unknown bicyclic P,S-heterocycles containing fused thiopyran and phosphinine rings. The stereochemical structures of two of the obtained (4+2)-cycloadducts were unambiguously assigned by means of the X-ray single-crystal analysis. Based on these assignments, a concerted mechanism of the hetero-Diels-Alder reaction via the preferred endo approach of the heterodiene from the less hindered P=O side of the phosphininone molecule is postulated to explain the established rac-(4RS,8SR,9SR,10SR)-configured (4+2)-cycloadducts isolated as major products.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2024 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Suiza
Texto completo
Añadir a Mi BVS
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2024 Tipo del documento: Article País de afiliación: Polonia Pais de publicación: Suiza